The crazyness of the best country in the world. "I rolled the dice!". This looks insane to any non-American.

In the future, you should just look into temporary insurance. Almost every insurer offers temporary plans that you can buy for 1-6 months of coverage to handle a gap between jobs. Unless you have some reason to keep your COBRA coverage (e.g. regular appointments for a chronic condition), the temp insurance acts as good emergency coverage and for very small amounts (last time I did it, ~$250 total for 3 months coverage)

Yeah, most people don't realize that you have 90 days to elect COBRA retroactively after you leave a job. They'll reimburse all your expenses incurred during that time period under the program as if you'd had it the whole time. Once you pay the premiums, of course.

So you basically get 90 days "free" COBRA, but your deductible is 1, 2 or 3 months premiums.

It can seem expensive if you ignored the compensation your employer was paying while you were employed.